In 1955, Spanish architect Josep Sert in collaboration with structural artists Felix Candela designed a pilot plan for the city of Havana, Cuba. Part of the plan included a Presidential Palace which consisted of 140 8-sided concrete umbrellas arranged in a 104-m x 104-m grid. While much is known about Candelas prolific 4-sided umbrella, there hasnt been much (if any) investigation into the behavior of the 8-sided umbrella. This research delves into trying to understand 8-sided umbrellas geometrically, mathematically, and structurally. In order to accomplish this, two case studies were used: the 8-sided umbrellas of the Presidential Palace and the 8-sided umbrellas of the Jamaica Market. Additionally, 4-sided versions of both studies were created to serve as a comparison between the 4-sided and 8-sided umbrellas. Based on the results of the models analyzed in SAP2000, the 8-sided umbrella performs worse structurally than the 4-sided umbrella due to high tension regions that developed along the fold of the hypar. Preliminary 2D analyses confirm the increased tension in those areas. Future work would have to be done to determine the effects of steel reinforcement in optimized locations, the column/umbrella interaction, and effects of wind/earthquake if it is to be considered as a viable design option in the future.